Fundraising while Homeless

Homeless?! Are you serious?! I’m a scrappy, ass-busting, well liked person. Man, did these stars align in the oddest of ways.

Chance I’ll be in national forest tonight with my cat in the Rav4: 99.999%.

Not only did my last two ventures fail, the speed of the current project is half what I need it to be to get revenue flowing, and that’s now impacted by the old Maslow hierarchy. Add to it I need electricity to write code.

I’d be in the forest already if it weren’t for bitcoin, though my wallet is just shy of empty. I’ve got enough for one more night in a hotel, and I’ll save that for next week because I have to shower before I start pitching. (Yeah. Fundraising while homeless. There’s a confidence enhancer.)

My savings depleted despite eating ramen for a bloody year, I’ve got hundreds of dollars to my name. (Personal income during the last three startup years: around $20k.)

I haven’t sat on my hands even for a second, though did take time off (4 weeks in Feb) to mourne the last shutdown because I really thought we had it made. Even then I wrote, did some RebootHQ self-guided classes, went on a podcast to explain how to fail, came on StartupsAnon to pep-talk others, and more.

Applied for *dozens* of jobs since March. (More than 100, I bet.) These ranged from underqualified to amazing fits to overqualified. Results: 3 interviews and zero offers. Are former CEO’s blacklisted or something? (And what the hell is up with _dead silence_ as an HR policy after starting a dialogue? Say “no”. Even “hell, no” please.)

To support my job hunting effort I studied new technologies and wrote technical blog posts about ’em which even got traffic.

I’m not even a kid. I have 30 years of professional experience and LinkedIn recommendations I didn’t solicit.

(Yep. I’ve already exhausted the friend’s/family extra room thing, plus it’s got a different world of weight when you’re near 50y old.)

Reached out for contract/consulting work throughout. Nothing.

I helped two other startups which both shut their doors in the same 6 months.

I should be depressed as hell but the funny thing is I wrote software which manages moods. Not even looking for sympathy here, though advice or ideas won’t hurt my feelings.

Lessons for myself/others:
– prep twice as much for the down swing as expected

PS- I think one is more likley to be homeless as an older founder because you don’t have the support of family and friends that younger founders do.

It generally takes three years of doing business full time before you generate sustainable revenue. So the good news is, you’ll be alright. But the bad news…holy cow being homeless sucks.

I would try to offer a product you can charge for right away, instead of focusing on investors. If it is CONVENIENT to pitch investors, then do so. But it’s generally more effort to get investors than it is to get customers.

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